Networking When You Hate Talking to Strangers

The power of serendipity is hot in business circles. Silicon Valley campuses have been constructed to foster more “random collisions.” One key to creativity, many thinkers say, is unexpected interactions. “Create spaces where you’re wandering around and exposing yourself to new people,” John Hagel of Deloitte’s Center for the Edge told me in an interview. And venture capitalist Anthony Tjan and his colleagues conducted an expansive survey of entrepreneurs that revealed a quarter of them self-identified as lucky and traced their success to embracing serendipitous encounters.

All that is well and good – for people who don’t mind talking to strangers. But as an introvert, one of the situations I hate most is making small talk with people I don’t know. Here’s how I’ve managed to strike the balance between meeting new people – and being exposed to interesting new ideas – and not having to initiate awkward conversations.

Make them come to you. The very best solution I’ve found for uncomfortable events where you don’t know anyone is arranging to be the speaker. That might seem paradoxical, but there’s a difference between introversion and shyness; I’m actually far more comfortable on a stage in front of hundreds of people than I am chatting in a small group of folks I don’t know. I’m getting ready to launch an 11-city tour for my new book Stand Out, which presents the perfect solution: when you’re the speaker, people approach you, and there’s a ready-made topic of conversation.

Bring a friend. When you have a “wingman” at your side to help highlight your accomplishments at networking events, it can give you the confidence you need to approach others and break into conversations. Additionally, your friend likely knows people in the room that you don’t, and vice versa, so you can trade “warm introductions” and connect with new people. If you or your company is hosting the event, you can also encourage your friends to bring guests that they think you should meet. Just avoid the temptation to use your friend as a crutch and spend the evening talking with them — that defeats the purpose of meeting new people.

Have a few opening lines ready. The hardest part of interacting with a stranger is the opening. How do you get started? What do you say? That was the challenge facing a coaching client of mine, a talented executive from the West Coast. She frequently attended high-powered alumni events but wasn’t sure where to begin the conversation. We developed a few questions she felt comfortable using that didn’t sound hackneyed, but opened the door to a more substantive discussion. They don’t have to be profound; the goal is to kickstart a dialogue. Possibilities include:

What’s the coolest thing you’re working on right now?

How do you spend most of your time?

How did you hear about the event?

When there’s a common tie, such as alumni group: What year did you graduate/what house or dorm did you live in?

And when nothing else works, I’ve often simply said, “I don’t know anyone here. Can I talk to you?” No one has ever said no.

Research in advance. Finally, it’s easier to talk to someone if they don’t feel like a stranger. Even if you haven’t met them in person before, having some background information about them can suggest possible topics of conversation. You don’t have to become a stalker; educated guesses and light online research can carry you pretty far. For instance, most fundraisers have a host committee listed on the invitation. If you want to make the experience more pleasant, you can quickly Google them and see if anyone seems particularly interesting, or look for commonalities you can bring up, such as having attended the same college or living in the same neighborhood. Similarly, if you’re attending an event organized by a professional association, it’s likely that many of their board and advisory board members will be in attendance, and you can almost always find that information on the organization’s website.

Talking to strangers will probably never be comfortable for me. It’s exhausting for me when an airplane seatmate starts chattering, or a taxi driver wants to know too much about my day. But with these strategies, it’s possible to make just a little more room for serendipity in our lives.